research communications Crystal structure and theoretical study of N,N-bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]- oxazol-3-yl)methyl]-2-phenylethanamine

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1 research communications ISSN Crystal structure and theoretical study of N,N-bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]- oxazol-3-yl)methyl]-2-phenylethanamine Abdullah Aydın, a * Zeynep Soyer, b Mehmet Akkurt c and Orhan Büyükgüngör d Received 16 March 2018 Accepted 18 April 2018 a Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, Kastamonu, Turkey, b Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, Izmir, Turkey, c Department of Physics, Faculty of Sciences, Erciyes University, Kayseri, Turkey, and d Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey. *Correspondence aaydin@kastamonu.edu.tr Edited by M. Weil, Vienna University of Technology, Austria Keywords: crystal structure; 2,3-dihydro-1,3- benzoxazole ring; semi-empirical CNDO/2 method; HOMO; LUMO. CCDC reference: Supporting information: this article has supporting information at journals.iucr.org/e In the molecular structure of the title compound, C 24 H 19 Cl 2 N 3 O 4, the three C atoms of the central N,N-dimethylmethanamine moiety are bonded to the N atoms of the two 5-chloro-1,3-benzoxazol-2(3H)-one groups and to the methyl C atom of the methylbenzene group. One of the nine-membered 2,3-dihydro-1,3- benzoxazole rings and the phenyl ring are almost parallel to each other, making a dihedral angle of 5.30 (18), but they are almost normal to the mean plane of the other nine-membered 2,3-dihydro-1,3-benzoxazole ring, subtending dihedral angles of (16) and (18), respectively. The crystal structure features C HO hydrogen bonds and stacking interactions [centroid-to-centroid distances = (19) Å, slippage = and (16) Å, and slippage = Å]. 1. Chemical context 2(3H)-Benzoxazolone is a privileged lead molecule for the design of potential bioactive agents, and its derivatives have been shown to posses a broad spectrum of bioactive properties such as anti-hiv (Deng et al., 2006), anticancer (Ivanova et al., 2007), analgesic (Ünlü et al., 2003), anti-inflammatory (Köksal et al., 2005), antinociceptive (Önkol et al., 2001), antimicrobial (Köksal et al., 2002), anticonvulsant (Ucar et al., 1998), antimalarial (Courtois et al., 2004) and human leukocyte MPO clorinating inhibitor activities (Soyer et al., 2005). In this context, we have investigated another benzoxazolone derivative with formula C 24 H 19 Cl 2 N 3 O 4, and report here its synthesis, molecular, crystal and theoretical structures. Acta Cryst. (2018). E74,

2 research communications Table 1 Comparison of experimental (X-ray) and theoretical (CNDO/2) bond lenghts and angles (Å, ) for the title compound. Bond X-ray CNDO/2 Figure 1 View of the title molecule with the atom-numbering scheme. Displacement ellipsoids for non-h atoms are drawn at the 30% probability level. 2. Structural commentary Cl1 C (3) Cl2 C (3) O1 C (3) O1 C (3) O2 C (3) O3 C (3) O3 C (4) O4 C (4) N1 C (3) N1 C (3) N1 C (3) N2 C (4) N2 C (4) N2 C (4) N3 C (3) N3 C (4) N3 C (3) C17 C (4) C18 C (4) C8 N2 C (2) C8 N2 C (19) C9 N2 C (2) Cl1 C4 C (19) Cl1 C4 C (2) O1 C7 O (3) O2 C7 N (3) N1 C8 N (2) N2 C9 N (2) O3 C10 O (3) O4 C10 N (3) Cl2 C14 C (2) Cl2 C14 C (2) N2 C17 C (2) C17 C18 C (2) C18 C19 C (3) C18 C19 C (3) The central part of the title molecule (Fig. 1) comprises an N,N-dimethylmethanamine unit whose three carbon atoms are bonded to the N atoms of the two 5-chloro-1,3-benzoxazol-2(3H)-one moieties and to the methyl carbon atom of the methylbenzene group. The nine-membered 2,3-dihydro-1,3- benzoxazole ring (N3/O3/C10 C16) and the phenyl ring (C19 C24) are almost parallel to each other, making a dihedral angle of 5.30 (18). These two entities are almost normal to the mean plane of the other 2,3-dihydro-1,3-benzoxazole ring (N1/ O1/C1 C7), subtending dihedral angles of (16) and (18), respectively. The C7 N1 C8 N2, N2 C9 N3 C16, N2 C17 C18 C19 and C17 C18 C19 C24 torsion angles are 90.7 (3), 75.6 (3), 63.6 (3) and (4), respectively. The bond lengths and angles of the title molecule (Table 1) are normal and correspond to those observed in related benzoxazolone derivatives (Aydın et al., 2004, 2012, 2017; Allen et al., 1987). 3. Supramolecular features The crystal structure features weak intermolecular C HO hydrogen bonds (Table 2, Fig. 2) between a methylene group and a carbonyl O atom of a neighbouring molecule. stacking interactions [Cg1Cg3 ii = (19) Å, slippage = Å and Cg2Cg2 iii = (16) Å, slippage = Å, symmetry codes: (ii) x, 1+y, z, (iii) 1 x,1 y,1 z, where Cg1, Cg2 and Cg3 are the centroids of the O3/N3/C10/C11/C16 2,3-dihydro-1,3-oxazole ring, the C1 C6 benzene ring and the C19 C24 phenyl ring, respectively] additionally consolidate the crystal packing. Figure 2 A view of the crystal packing in the title structure, showing the C HO hydrogen bonding and stacking interactions. H atoms not involved in hydrogen bonds are omitted for the sake of clarity. [Symmetry codes: (a) x 1, y, z; (b) x, y 1, z; (c) 1 x, 1 y, 1 z.] Table 2 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA C8 H8AO4 i (4) 114 Symmetry code: (i) x 1; y; z. 758 Aydın et al. C 24 H 19 Cl 2 N 3 O 4 Acta Cryst. (2018). E74,

3 research communications 4. Theoretical calculations Semi-empirical molecular orbital (MO) calculations of the title molecule were carried out using the CNDO/2 method (Pople & Segal, 1966). It is based on the Complete Neglect of Differential Overlap integral approximation. The semiempirical CNDO/2 parameterization is widely used to derive bond lengths, bond angles, torsion angles, atom charges, HOMO and LUMO energy levels, dipole moments, polarizability, etc. The spatial view of the title compound calculated as a closed-shell in a vacuum at 0 K is shown in Fig. 3. In the title molecule, the calculated charges on the Cl1, Cl2, O1, O2, O3, O4, N1, N2 and N3 atoms are 0.164, 0.226, 0.424, 0.228, 0.431, 0.117, and e, respectively. The calculated dipole moment is about Debye. The HOMO and LUMO energy levels are and ev, respectively. The calculated bond lengths and angles of the title molecule are consistent with those obtained by X-ray structure determination within error limits (Table 1). Looking at Figs. 1 and 3, the experimental and calculated conformations appear to be quite different. This is supported by the torsion angles N1 C8 N2 C17 [experimental 70.5 (3), calculated ], N1 C8 N2 C9 [ 62.8 (3), ], N2 C17 C18 C19 [ 63.6 (3), ], C18 C17 N2 C8 [84.1 (3), ] and C9 N2 C17 18 [143.5 (2), ]. The small differences between the theoretical and experimental results are due to the calculations being in a vacuum and at 0 K. 5. Synthesis and crystallization 4-Chloro-2-aminophenol (10 mmol), urea (50 mmol) and 37% wt HCl (2.5 ml) were irradiated (300 W, 413 K) for 15 min in a microwave oven. After completion of the reaction (monitored with TLC), water (10 ml) was added to the reaction mixture and stirred at room temperature for 1 h. The resulting precipitate was filtered and washed with water. After drying the precipitate, crystallization from ethanol water (1:1 v/v) yielded 5-chloro-2(3H)-benzoxazolone. This compound Table 3 Experimental details. Crystal data Chemical formula C 24 H 19 Cl 2 N 3 O 4 M r Crystal system, space group Triclinic, P1 Temperature (K) 296 a, b, c (Å) (5), (5), (15),, ( ) (5), (5), (5) V (Å 3 ) (14) Z 2 Radiation type Mo K (mm 1 ) 0.33 Crystal size (mm) Data collection Diffractometer Stoe IPDS 2 Absorption correction Integration (X-RED32; Stoe & Cie, 2002) T min, T max 0.901, No. of measured, independent and 15409, 4604, 2261 observed [I > 2(I)] reflections R int (sin /) max (Å 1 ) Refinement R[F 2 >2(F 2 )], wr(f 2 ), S 0.043, 0.089, 0.87 No. of reflections 4604 No. of parameters 298 H-atom treatment H-atom parameters constrained max, min (e Å 3 ) 0.13, 0.17 Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXS97 and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows and WinGX (Farrugia, 2012) and PLATON (Spek, 2009). (2 mmol) was dissolved in methanol (5 ml). Phenethylamine (2 mmol) and 37% wt formalin (2.5 mmol) were added to this solution. The mixture was then stirred vigorously for 1 h. The resulting precipitate was filtered and washed with cold methanol. The crude product was recrystallized from methanol, yield 40%; m.p. 427 K. IR max (FTIR/ATR): 3062, 2862, 1769, 1038 cm 1 ; 1 H NMR (CDCl 3 ): 2.79 (2H, t, J = 6.8 Hz, NCH 2 CH 2 ), 3.14 (2H, t, J = 7.0 Hz, CH 2 CH 2 -phenyl) 4.90 (4H, s, 2 CH 2 ), (11H, m, Ar-H) ppm; MS (ESI) m/z (%): 315 (100), 317 (37), 484 (M + H, 3), 486 (M + H + 2, 1). 6. Refinement Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C H = 0.93 (aromatic) and 0.97 (methylene) Å and U iso = 1.2U eq (C). Figure 3 The molecular structure of the title compound calculated using the CNDO/2 method. Acknowledgements The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). Acta Cryst. (2018). E74, Aydın et al. C 24 H 19 Cl 2 N 3 O 4 759

4 research communications References Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1 19. Aydın, A., Önkol, T., Akkurt, M., Büyükgüngör, O. & Ünlü, S. (2004). Acta Cryst. E60, o244 o245. Aydın, A., Soyer, Z., Akkurt, M. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1544 o1545. Aydın, A., Soyer, Z., Akkurt, M. & Büyükgüngör, O. (2017). Univ. J. Phys. Appl. 11, Courtois, M., Mincheva, Z., Andreu, F., Rideau, M. & Viaud- Massuard, M. C. (2004). J. Enzyme Inhib. Med. Chem. 19, Deng, B. L., Cullen, M. D., Zhou, Z., Hartman, T. L., Buckheit, R. W. Jr, Pannecouque, C., Clercq, E. D., Fanwick, P. E. & Cushman, M. (2006). Bioorg. Med. Chem. 14, Farrugia, L. J. (2012). J. Appl. Cryst. 45, Ivanova, Y., Momekov, G., Petrov, O., Karaivanova, M. & Kalcheva, V. (2007). Eur. J. Med. Chem. 42, Köksal, M., Gökhan, N., Erdoğan, H., Ozalp, M. & Ekizoğlu, M. (2002). II Farmaco. 57, Köksal, M., Gökhan, N., Küpeli, E., Yesilada, E. & Erdoğan, H. (2005). Arch. Pharm. Pharm. Med. Chem. 338, Önkol, T., Ito, S., Yıldırım, E., Erol, K. & Şahin, M. F. (2001). Arch. Pharm. Pharm. Med. Chem. 334, Pople, J. A. & Segal, G. A. (1966). J. Chem. Phys. 44, Sheldrick, G. M. (2008). Acta Cryst. A64, Soyer, Z., Baş, M., Pabuçcuoğlu, A. & Pabuçcuoğlu, V. (2005). Arch. Pharm. Chem. Life Sci. 338, Spek, A. L. (2009). Acta Cryst. D65, Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Ucar, H., Van derpoorten, K., Cacciaguerra, S., Spampinato, S., Stables, J. P., Depovere, P., Isa, M., Masereel, B., Delarge, J. & Poupaert, J. H. (1998). J. Med. Chem. 41, Ünlü, S., Önkol, T., Dündar, Y., Ökçelik, B., Küpeli, E., Yeşilada, E., Noyanalpan, N. & Şahin, M. F. (2003). Arch. Pharm. Pharm. Med. Chem. 336, Aydın et al. C 24 H 19 Cl 2 N 3 O 4 Acta Cryst. (2018). E74,

5 supporting information [ Crystal structure and theoretical study of N,N-bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazol-3-yl)methyl]-2-phenylethanamine Abdullah Aydın, Zeynep Soyer, Mehmet Akkurt and Orhan Büyükgüngör Computing details Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009). N,N-Bis[(5-chloro-2-oxo-2,3-dihydrobenzo[d]oxazol-3-yl)methyl]-2-phenylethanamine Crystal data C 24 H 19 Cl 2 N 3 O 4 M r = Triclinic, P1 Hall symbol: -P 1 a = (5) Å b = (5) Å c = (15) Å α = (5) β = (5) γ = (5) V = (14) Å 3 Data collection Stoe IPDS 2 diffractometer Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus Plane graphite monochromator Detector resolution: 6.67 pixels mm -1 ω scans Absorption correction: integration (XRED-32; Stoe & Cie, 2002) Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 298 parameters 0 restraints Z = 2 F(000) = 500 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from reflections θ = µ = 0.33 mm 1 T = 296 K Plate, light yellow mm T min = 0.901, T max = measured reflections 4604 independent reflections 2261 reflections with I > 2σ(I) R int = θ max = 26.5, θ min = 1.8 h = 9 9 k = 9 9 l = Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained sup-1

6 w = 1/[σ 2 (F o2 ) + (0.0273P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.13 e Å 3 Δρ min = 0.17 e Å 3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wr and all goodnesses of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The observed criterion of F 2 > 2sigma(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Cl (11) (11) (3) (3) Cl (13) (15) (4) (4) O (3) (3) (8) (7) O (3) (3) (9) (8) O (3) (3) (8) (8) O (3) (4) (9) (10) N (3) (3) (9) (7) N (3) (3) (8) (8) N (3) (3) (9) (8) C (3) (4) (11) (9) C (4) (4) (11) (10) C (3) (4) (11) (9) C (3) (4) (11) (9) C (3) (4) (11) (9) C (3) (4) (10) (9) C (4) (4) (12) (11) C (4) (4) (10) (9) C (4) (4) (11) (10) C (4) (4) (13) (11) C (4) (4) (12) (10) C (4) (5) (13) (11) C (5) (5) (12) (11) C (4) (4) (12) (11) C (4) (4) (12) (10) C (4) (4) (10) (9) C (4) (4) (11) (10) C (5) (4) (11) (11) C (5) (4) (13) (11) C (6) (5) (15) (14) C (8) (6) (19) (2) C (11) (7) (2) (3) C (9) (6) (2) (2) sup-2

7 C (6) (5) (15) (14) H * H * H * H8A * H8B * H9A * H9B * H * H * H * H17A * H17B * H18A * H18B * H * H * H * H * H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Cl (5) (5) (5) (4) (4) (4) Cl (6) (9) (6) (6) (5) (5) O (12) (12) (12) (10) (9) (10) O (16) (13) (13) (12) (11) (11) O (11) (16) (13) (12) (10) (12) O (15) (2) (14) (15) (12) (14) N (13) (13) (12) (11) (10) (10) N (13) (14) (12) (12) (10) (10) N (14) (15) (13) (12) (10) (11) C (15) (17) (16) (14) (12) (13) C (17) (19) (16) (15) (13) (14) C (15) (19) (14) (15) (12) (14) C (15) (16) (16) (13) (12) (13) C (14) (16) (15) (13) (11) (12) C (14) (17) (15) (13) (11) (13) C (19) (2) (18) (17) (14) (15) C (16) (18) (14) (15) (12) (13) C (17) (18) (15) (15) (13) (13) C (19) (2) (19) (17) (15) (17) C (17) (18) (17) (15) (13) (14) C (2) (2) (19) (19) (15) (17) C (2) (2) (16) (19) (16) (15) C (19) (2) (17) (17) (14) (15) C (16) (19) (16) (15) (13) (14) sup-3

8 C (16) (16) (15) (14) (13) (12) C (17) (18) (15) (16) (13) (13) C (2) (19) (17) (18) (16) (15) C (2) (17) (18) (18) (18) (14) C (3) (2) (2) (2) (2) (19) C (5) (3) (3) (3) (3) (2) C (7) (3) (3) (4) (4) (2) C (5) (3) (3) (3) (3) (3) C (3) (2) (2) (2) (2) (18) Geometric parameters (Å, º) Cl1 C (3) C15 C (4) Cl2 C (3) C17 C (4) O1 C (3) C18 C (4) O1 C (3) C19 C (6) O2 C (3) C19 C (6) O3 C (3) C20 C (5) O3 C (4) C21 C (10) O4 C (4) C22 C (10) N1 C (3) C23 C (6) N1 C (3) C2 H N1 C (3) C3 H N2 C (4) C5 H N2 C (4) C8 H8A N2 C (4) C8 H8B N3 C (3) C9 H9A N3 C (4) C9 H9B N3 C (3) C12 H C1 C (3) C13 H C1 C (4) C15 H C2 C (4) C17 H17A C3 C (4) C17 H17B C4 C (3) C18 H18A C5 C (4) C18 H18B C11 C (4) C20 H C11 C (4) C21 H C12 C (5) C22 H C13 C (5) C23 H C14 C (4) C24 H C1 O1 C (2) C19 C20 C (4) C10 O3 C (2) C20 C21 C (5) C6 N1 C (2) C21 C22 C (4) C6 N1 C (2) C22 C23 C (6) C7 N1 C (2) C19 C24 C (4) C8 N2 C (2) C1 C2 H C8 N2 C (19) C3 C2 H sup-4

9 C9 N2 C (2) C2 C3 H C9 N3 C (2) C4 C3 H C9 N3 C (2) C4 C5 H C10 N3 C (2) C6 C5 H O1 C1 C (2) N1 C8 H8A O1 C1 C (2) N1 C8 H8B C2 C1 C (2) N2 C8 H8A C1 C2 C (2) N2 C8 H8B C2 C3 C (2) H8A C8 H8B Cl1 C4 C (19) N2 C9 H9A Cl1 C4 C (2) N2 C9 H9B C3 C4 C (2) N3 C9 H9A C4 C5 C (2) N3 C9 H9B N1 C6 C (2) H9A C9 H9B N1 C6 C (2) C11 C12 H C1 C6 C (2) C13 C12 H O1 C7 O (3) C12 C13 H O1 C7 N (2) C14 C13 H O2 C7 N (3) C14 C15 H N1 C8 N (2) C16 C15 H N2 C9 N (2) N2 C17 H17A O3 C10 O (3) N2 C17 H17B O3 C10 N (2) C18 C17 H17A O4 C10 N (3) C18 C17 H17B O3 C11 C (3) H17A C17 H17B O3 C11 C (2) C17 C18 H18A C12 C11 C (3) C17 C18 H18B C11 C12 C (3) C19 C18 H18A C12 C13 C (3) C19 C18 H18B Cl2 C14 C (2) H18A C18 H18B Cl2 C14 C (2) C19 C20 H C13 C14 C (3) C21 C20 H C14 C15 C (3) C20 C21 H N3 C16 C (3) C22 C21 H N3 C16 C (3) C21 C22 H C11 C16 C (2) C23 C22 H N2 C17 C (2) C22 C23 H C17 C18 C (2) C24 C23 H C18 C19 C (3) C19 C24 H C18 C19 C (3) C23 C24 H C20 C19 C (3) C7 O1 C1 C (3) O1 C1 C2 C (3) C7 O1 C1 C6 2.3 (3) C2 C1 C6 N (3) C1 O1 C7 N1 3.4 (3) C2 C1 C6 C5 0.7 (4) C1 O1 C7 O (3) O1 C1 C6 C (2) C11 O3 C10 N3 1.7 (3) C1 C2 C3 C4 0.6 (4) C11 O3 C10 O (3) C2 C3 C4 Cl (2) sup-5

10 C10 O3 C11 C (3) C2 C3 C4 C5 1.3 (4) C10 O3 C11 C (3) C3 C4 C5 C6 1.6 (4) C8 N1 C7 O (2) Cl1 C4 C5 C (2) C6 N1 C7 O1 3.3 (3) C4 C5 C6 N (3) C6 N1 C8 N (3) C4 C5 C6 C1 1.3 (4) C7 N1 C8 N (3) C12 C11 C16 C (5) C7 N1 C6 C1 1.9 (3) C12 C11 C16 N (3) C8 N1 C6 C (3) O3 C11 C12 C (3) C7 N1 C6 C (3) C16 C11 C12 C (5) C8 N1 C6 C5 4.3 (5) O3 C11 C16 N3 1.1 (3) C6 N1 C7 O (3) O3 C11 C16 C (2) C8 N1 C7 O2 3.9 (5) C11 C12 C13 C (5) C17 N2 C8 N (3) C12 C13 C14 C (5) C9 N2 C17 C (2) C12 C13 C14 Cl (3) C8 N2 C9 N (2) Cl2 C14 C15 C (2) C9 N2 C8 N (3) C13 C14 C15 C (4) C8 N2 C17 C (3) C14 C15 C16 C (4) C17 N2 C9 N (3) C14 C15 C16 N (3) C9 N3 C10 O (2) N2 C17 C18 C (3) C16 N3 C10 O3 1.1 (3) C17 C18 C19 C (4) C10 N3 C16 C (3) C17 C18 C19 C (4) C9 N3 C16 C (5) C18 C19 C20 C (3) C9 N3 C10 O4 5.6 (5) C24 C19 C20 C (5) C16 N3 C10 O (3) C18 C19 C24 C (3) C10 N3 C16 C (3) C20 C19 C24 C (5) C10 N3 C9 N (3) C19 C20 C21 C (6) C16 N3 C9 N (3) C20 C21 C22 C (7) C9 N3 C16 C (2) C21 C22 C23 C (7) C6 C1 C2 C3 0.3 (4) C22 C23 C24 C (6) O1 C1 C6 N1 0.3 (3) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C8 H8A O4 i (4) 114 C9 H9A O (4) 102 C17 H17A N (3) 105 Symmetry code: (i) x 1, y, z. sup-6